This invention relates to the reaction of xylene with chlorine gas to produce .alpha.-chloroxylenes. In particular, it relates to performing the reaction in a solvent of toluene, ring halogenated toluene, benzotrichloride (BTC), ring halogenated BTC, benzotrifluoride (BTF), ring halogenated BTF, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluorometaxylene (HFMX), .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluoroparaxylene (HFPX), or a mixture thereof to minimize ring chlorination. .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-Hexachloroparaxylene (HCPX) is an important chemical intermediary used to make herbicides and other products. High purity (&gt;99%) HCPX is required for many applications. HCPX can be made by reacting p-xylene with chlorine gas in a solvent. For example, JP6-340562 discloses that process using a base and a solvent of a chlorinated benzotrifluoride, such as parachlorobenzotrifluoride, to produce 99% pure HCPX. Washing to remove impurities, however, was required to obtain that level of purity. The use of a base and the subsequent washing step add to the cost of producing the HCPX.